BU-48

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BU-48
Identifiers
  • N-Cyclopropylmethyl-[7α,8α,2',3']-cyclohexano-1'[S]-hydroxy-6,14-endo-ethenotetrahydronororipavine
PubChem CID
ChemSpider
Chemical and physical data
FormulaC27H33NO4
Molar mass435.554 g/mol g·mol−1
3D model (JSmol)
  • CO[C@]12C=C[C@@]3([C@H]4[C@@H]1[C@H](CCC4)O)[C@H]5Cc6ccc(c7c6[C@]3([C@H]2O7)CCN5CC8CC8)O
  • InChI=1S/C27H33NO4/c1-31-27-10-9-25(17-3-2-4-18(29)22(17)27)20-13-16-7-8-19(30)23-21(16)26(25,24(27)32-23)11-12-28(20)14-15-5-6-15/h7-10,15,17-18,20,22,24,29-30H,2-6,11-14H2,1H3/t17-,18+,20-,22-,24-,25-,26+,27-/m1/s1
  • Key:LMFRYUPWVALVRA-QDFTYCMYSA-N
  (verify)

BU-48 is a drug that is used in scientific research. It is from the oripavine family, related to better-known drugs such as etorphine and buprenorphine.

The parent compound from which BU-48 was derived (with N-methyl rather than methylcyclopropyl on the nitrogen and lacking the aliphatic hydroxyl group) is a powerful μ-opioid agonist 1000x more potent than morphine,[1] but in contrast BU-48 has only weak analgesic effects and instead acts primarily as a δ-opioid agonist. Its main effects are to produce convulsions,[2] but it may also have antidepressant effects.[3]

References

  1. ^ Lewis JW, Bentley KW, Cowan A. Narcotic Analgesics and Antagonists. Annual Reviews in Pharmacology 1971;11:241-270.
  2. ^ Broom DC, Guo L, Coop A, Husbands S, Lewis JW, Woods JH, Traynor JR. BU48: A novel buprenorphine analogue that exhibits delta-opioid mediated convulsions but not delta-opioid-mediated antinociception in mice. Journal of Pharmacology and Experimental Therapeutics 2000 Sep; 294(3): 1195–1200. PMID 10945877
  3. ^ Broom DC, Jutkiewicz EM, Rice KC, Traynor JR, Woods JH. Behavioral effects of delta-opioid receptor agonists: potential antidepressants? Japanese Journal of Pharmacology. 2002 Sep;90(1):1-6. doi:10.1254/jjp.90.1 PMID 12396021